Jennifer's Big Night Out Ch. 01

Dan didn't recognize the number and thought he'd just let it go to voicemail. But he suffered from FOMO -- the fear of missing out. He answered. "Hi this is Dan".

From the other side of the phone there was a squeal of delight, "Finally. I've been through about a million numbers hoping I'd eventually land on yours. Sorry it took so long; I've been away but I wanted to see if you were still ready to honour your promise. You remember the one you made to me.......Jennifer."

Dan knew from the first words who this was. He was secretly delighted she'd called. He couldn't stop smiling. But an anxiety grabbed him and he didn't quite know what to do.

"Beth, I'm delighted to hear from you. I've wanted you to call and to be honest I'm not quite sure how you got my number. But there's a problem. I know I promised to go on a date with you, but when I left your Mum's house after the party...."

"Where you made a gorgeous bunny girl waitress"

"After the party," Dan continued, delighted with the compliment, "Your mum, Mistress Caroline, told me that if I saw you outside of that house, she'd cut my dick off. Beth.." Dan swallowed, "I don't think she was joking."

Beth was silent for a second. A second was about all she could manage. "I'd don't think she was serious Jen. She wouldn't hurt a pussy cat -- or a bunny rabbit." Beth laughed at her own joke and Dan liked it when she called him Jen. "Anyway, she doesn't need to know. I got your number from ringing numbers that had called Mum. I swiped her phone for a while. I know naughty huh? Please can you come to mine and we'll get you ready for a night on the town? Oh, please come Jen. Please. It'll be a real laugh and I'd really like to see you again. I really would."

"Whose we?" asked Dan more than a little concerned.

"What?" Dan could tell Beth was stalling.

"You said we'll get you ready. Who is we?"

Beth could tell there was worry in his voice. Or was it actually fear. "Well Tanya will be there; you remember her from the party? Wasn't she gorgeous? She has that wonderful red hair and those gorgeous eyes. She's always getting hit on while we're out. She likes you and thinks a night out would be fun."

"C'mon Beth."

"Yes, Jayne will be there. Look I know it didn't go well the last time. But she'd had too much to drink and I'll keep an eye on her this time. I really will. I won't let her do anything mean to you -- unless you want her too." She giggled again at her joke and without taking a breath continued, "Anyway she hasn't stopped talking about the party and about you. I know this might sound crazy but I think she might have a little crush on Jennifer. But all that's kind of irrelevant. Because I want to see you. I like you Jennifer. You're sweet and pretty and were so vulnerable. I want to see you again -- away from the party -- away from Mistress Caroline. I want to see you. And you did promise -- remember?"

Dan remembered. He was strapped to a bed in his bunny girl outfit when Beth snuck into the room and gave him a hand job and stopped as he was right on the edge and made him agree to a night out with her dressed as Jennifer. Dan was so turned on, he agreed immediately and blew his load all over her hand and inside his bunny suit. Beth made him lick her hand clean. It was the first time he'd tasted his own cum. Something he did now on a regular basis. Particularly when he thought back to the night when he served as a bunny girl waitress.

"I'm still worried about your Mum. She sounded pretty serious when she threatened to cut my dick off. And she looked pretty serious too."

"She's threated all my boyfriends. But nothing's ever happened to them. She can't keep treating me like I'm twelve."

Dan thought the last part sounded like the sort of outburst a 12-year-old would make, but decided to let it slip.

"What do you have in mind?"

We thought you'd like to join us for a Hen party on Saturday."

"Beth that's crazy and it's just two days away."

"Less time for you to back out gorgeous. Join us for the Hen party -- come over to my place on Saturday afternoon. We'll get you all dolled up and we'll hit the town. Look, no-one's going to hurt you or force you to do anything you don't want to do. I'll keep Jayne in check this time I promise. It'll just be the girls, four sexy girls on the town. Only one will have a not so little secret tucked away in her silky panties."

Beth knew the buttons to push. Just like her mother. Dan wanted to do it. It sounded like fun. And as he stood at the entrance to his office where he'd gone to take the call, he was stiff in the silky panties he now wore as a matter of course every day.

"And you promise your mum won't find out."

"Scout's promise"

"Beth?"

"Mmm humm?"

"Were you ever in the Scouts."

"Nope."

They both laughed. Dan liked that. It was a moment of closeness, and intimacy. A shared joke.

He paused. Beth thought he was going to back out.

"Ok I'm in."

Beth squealed in delight. She was so loud Dan had to hold the phone away from his ear.

"As long as you promise Caroline will never find out. And you keep Jayne in check."

"Yes. Absolutely yes. And I will handle Jayne. I really will."

"Where do we meet?"

"It's the top floor apartment, number six."

"Yeah, but where? London is a big place Beth."

"You know where silly. Top floor of the same apartment block where Mum created the gorgeous Jennifer. See you around three. Bye sexy. Mmmmwhaaah."

Dan stared at the phone for a second. He knew the place she meant. It was a short walk from the Adult bookstore where he first encountered Caroline. It's where Dan was transformed into Jennifer and where she posed and pouted for picture spreads for Forced Femininity magazine. And where Jennifer had met the gorgeous Suzanne. Such a beautiful girl. But it turned out also had a cock. A cock Jennifer had sucked. The first time that had ever happened.

Caroline had introduced Dan to so many firsts, had realised so many of his fantasies: some acknowledged; some deeply hidden. And she had led Jennifer into a new life where she was actually happier and more confident than she had ever been. Dan enjoyed the benefits of that. He even seemed to smile more.

So, three o'clock on Saturday Jennifer would return to the scene of her first triumph. She wasn't sure if she was scared or excited, but her cock answered that question for her.

Dan couldn't sleep on Friday night. He was much too excited about what lay ahead. Putting aside that he thought Beth was gorgeous and sexy, the idea of being one of the girls on a girls' night out tormented him beyond belief. How many times had he thought of such a thing? Of being part of the girl's teams at school and wearing the uniform for the hockey team of blue shirt and little pink hockey skirt.

Of joining the girls at University in one of their sleepovers, slipping into to something satiny and slinky and just relaxing? Or joining the women from work on one of their spa days where they'd go for massages and facials and spend the rest of the day lazing by the pool in bikinis or really tight and lovely all in one swimsuit. Dan loved that idea. And now he'd get the chance to be one of the girls.

But he was anxious too. Did Beth see him the same way he viewed her, with some level of hope they could have a relationship? And was she really going to protect him? It really hadn't worked at her mother's party. Would her mother find out? And there always the question of Jayne. Could Beth really reign her in? Did Jayne remember she confessed to Jennifer she had a few moments with girls in her past?

All of this passed through Dan's brain and he wanked himself off at the thought of what lay ahead before falling into a restless sleep.

On Saturday afternoon Dan walked past the Adult bookstore, the place where he'd gone to buy something after work and ended up in a photoshoot. He retraced his steps of that night and found himself in front of a modern apartment block. It was just a couple of minutes before three.

He found the buzzer for apartment six. The name on it said Bellamy. He pushed it. It took a second or two then a familiar voice boomed out. "Jennifer, that had better be you."

Two young girls walked past but stopped just a few steps away from Dan. Beth spoke again "Jennifer can you hear me? Are you ready to look sexy and cute?" The girls laughed and waited for Dan to answer. God it was embarrassing.

"Hi Beth."

"Come on up sexy" and she pushed the buzzer to open to door. Dan dashed in, away from the girls. But one looked through the door and blew him a kiss. God, he hated the humiliation. God, he also loved the humiliation.

He walked past the apartment where the photoshoot had taken place and walked on up the stairs. He knocked gently on the door of apartment six. It was right at the top of the building. Beth opened the door. She looked amazing. Her hair fell over her shoulders, she was wearing a tight blue t-shirt with no bra. She had on a pair of pink shorts and was barefoot.

She gave Dan a huge smile 'Hey sexy. Oh my god I am so glad you're here." She gave Dan a hug he chose to believe was long and lingering. "Did you have any trouble finding the place? Of course you didn't. You've been downstairs before. Oh hell, listen to me. I guess I'm just excited. Oh we are going to have such a great night. Come one come in." And she waved her arm ushering Dan into the apartment.

The place was massive. It had huge floor to ceiling windows and seemed to take up the entire top floor. At one end of the room was a large screen TV and two large sofas that looked incredibly comfortable. The place was very classily furnished. The floors were bare wood, except where very expensive rugs lay. And at the other end of the room was a very modern kitchen with all the latest stainless-steel appliances.

"You live here?" said Dan slightly incredulously.

Yeah, it's handy for college. And for town."

"It must cost a fortune in rent? What are you studying? Alchemy."

Beth laughed and stuck out her tongue

"Mum owns it. She owns the whole building. First floor is her photo place and there's a kind of an office across from that. Then there's an old couple in 3 and a dick who thinks he's wonderful in 4. I keep asking Mum to get rid of him but he pays over the market rate for the place, so she won't kick him out. And here five and six have been knocked together to create this little place." Beth laughed again. Dan liked she was so relaxed around him."

"You live here alone?"

Why would you take advantage of me if I said yes?" Beth looked coyly at the floor and laughed. Dan stiffened at the thought. "No silly, Tanya shares with me. She has her own room before you set your dirty mind running and no we don't stage pillow fights. What is it with guys and the lesbian thing?" Beth smiled.

"So fancy a drink before we get started?"

"It's a bit early to hit the drink Beth?"

"I meant tea or coffee. What are you like?" She playfully punched Dan and then suddenly hugged him again. Dan felt himself grow. And turned himself to the side slightly so it wouldn't brush against Beth.

As they sat drinking Beth looked Dan all over. He tingled. "Are you smooth?"

"Top to tail."

"Clever girl" said Beth which unsettled Dan slightly as he felt he was projecting quite a strong boy mode, but then realised he was going out as a girl in a few hours. The first time out. And was hugely nervous and excited about it. Beth looked at him quizzically "Why do you do it?"

Dan was kinda shocked. No one had ever asked him directly why he dressed. And he wasn't sure he had a good answer.

"I don't know. I was attracted to my mum's clothes when I was little and it kind of grew from there. I've always fancied girls so it's not about attracting boys. When I got to my teens, I found out what it was called and realised that was me. I read the stories in the Sunday papers about cross dressers and trannies and they excited me. I once saw a feature in a magazine of a guy dressed as a Vegas showgirl and wanted so much to be dressed like that. And my auntie wore really sexy clothes, like leather skirts and tight business suits. And I fantasised she would dress me up. When I went to college, I bought some panties and a few skirts, but purged a couple of times. I would dress then get disgusted with myself. Then I found your mum's store and bought some magazines that covered my interests"

"Did you wank off thinking you were the girls or because you found them attractive".

Dan blushed furiously "A bit of both really. But I never liked pictures of girls with their cocks out. Kind of spoiled the illusion. And then I met your mum and she said she could make my fantasies come true."

"Do you want to transition, or get boobs or anything like that."

"No. Sorry. Pure fetish I guess."

"Was it a fantasy to suck a cock on someone like Suzanne." (You have to read Dan's 1st Adventure to get the reference)

Dan stumbled over his words. "That was, ....I never,...... I didn't." He took a deep breath. "I didn't know she had a cock. I kind of got caught up in the moment and your mum encouraged me and Suzanne kinda begged me. Given the situation, it seemed....." Dan let the silence sit. He looked at Beth. She smiled. "But I like girls. Honest. Beth, the only reason I'm here is because I like you. Your mum made it clear I shouldn't see you again, but I was willing to risk that."

Beth crossed the room and hugged Dan. "I'm kinda mixed up about how I feel about you. I think you are a very cute boy and I think you make a gorgeous girl. So I don't know. But thanks for being honest".

The door to the apartment opened and Beth shot back to her seat. "Hey there I'm back. Did Jennifer show up."

"She's right here but is looking a bit butch at the moment."

In walked Tanya, Beth's friend and roommate. Her gorgeous red hair was pulled up into a high ponytail and her eyes sparkled. She was a very good-looking girl. She wore a short leather jacket, a pink polo shirt and tight black jeans and high heeled boots. She carried a number of bags.

"I picked some things up for this young lady's transformation and a couple of bottles of wine to get the evening started." She walked over to Dan and hugged him. "Wow -- you're sexier than I remember but then I didn't see Jennifer's alter ego, just the sexy bunny girl."

"Tanya's going to transform you tonight."

"Oh I thought..." Dan left his thought hanging in the air.

"Tanya's a qualified beautician. That's how she paying her way through college. She'll do a much better job than I did."

"Smooth?" asked Tanya

"Head to toe" said Beth.

"Really?" said Tanya, staring at Dan's crotch. "I can't wait to see and I won't ask how you know" she said shooting a smile at her friend. "Right baby, go shower and I'll come and get you to start your makeover. I've got some ideas of what you'll look good in."

Dan wanted to be a typical boy with these two sexy girls but couldn't help stiffen at the thought of what lay ahead.

Dan stepped out of the shower to find Beth and Tanya standing in the bathroom. He quickly grabbed a towel, which made the girls laugh. "She's not little is she?" said Tanya flexing her little finger. Beth laughed.

"No and I've seen her full on. She's bigger than most of the boys I've dated."

"I'm not sure I have undies that will hold that in place under the dress I had planned. We might need to change things around."

"

What did you have in mind Tans? The silver dress like Jayne's?"

"No, the low-cut red one but I think we have to go with plan B."

"And make Jennifer....." Beth stopped short of finishing the sentence and looked at Tanya.

"Yes. What do you think?"

"Oh my god, I love it."

Dan, or Jennifer as he would soon become, had no idea what they were talking about but he wrapped the towel around his chest and stepped out of the shower.

"Right" said Tanya. To my bedroom. We have some work to do."

Dan walked into a large bedroom and made his way over to the make up table. Tanya followed, holding two glasses of white wine. "First I'm going to get your boobs in place. I was told you'd had forms glued on the last couple of times?" Dan nodded. "It's going to be a bit different this time." She walked over to a bag and produced what looked like the front of a ladies' torso with quite splendid boobs.

"I thought we'd go with a breast plate. It means you can go braless and be a little risqué. The red dress was low cut but what I have in mind now will work too as it has a lace front".

Tanya placed the breast place over Jennifer's head and made a few small adjustments. She then produced a make up bag and feathered around the very delicate edges so it all looked very natural. Jennifer stiffened and her excitement became very obvious in her towel. Tanya ignored it. Jennifer thought she looked embarrassed and let her finish was she was doing without saying a word.

"Sit", she ordered. And then started working on Jennifer's face. First was some moisturizer "You have great skin for a guy" said Tanya. Then worked on her eyes. She took her time getting the right shades and then worked away on foundation, blush and a very pretty pink lipstick.

Tanya stepped back and whistled slowly. "you know, one of my last assignments when I qualified in beauty therapy, I gave a guy a make over and made him look like a girl. I wish it had been you. I would have won top prize with your eyes and cheekbones. You look awesome."

She moved so Jennifer could see herself for the first time. Tanya was right. This was her third time being made up by a girl, but was by a long distance, the best. She looked astounding.

"I'm thinking blonde with some red streaks. I have the wig that will look fantastic on you".

She disappeared out of the room and as she came back, she was brushing out a hairpiece which Jennifer saw would go well over her shoulders and half way down her back. Tanya put some adhesive along the hairline then attached the wig. She brushed and styled it and then stood back.

"Seriously, I am very good at this."

"Shall we show Beth?"

"Nope, we'll wait till you have you in your undies then she'll see you when she brings in your dress."

Jennifer looked in the mirror. Her eyes had never looked so big or sparkly. Her lips were so full and round and her cheekbones looked amazing. With her hair and her boobs, she looked like someone Dan would lust after and Jennifer loved it.

Her dick was now standing straight up in the towel.

"That is a problem sweetie. The panties are cute but that's going to be very obvious." Tanya walked over and whispered into Jennifer's ear. "Can you keep a secret?"

Jennifer nodded, not trusting herself to speak at that moment. Tanya pulled down the towel and gently put her hand around Jennifer's erect member. "I can't have you spoiling all my hard work." She started to slowly to wank her off. "You've got to cum in the towel, not on your boobs or your face." Jennifer nodded again.

"And you can't tell the others I did this."

Jennifer knew she was close. She looked at Tanya but caught her eye and for some reason felt embarrassed and looked away. Jennifer didn't know if she was more worried Tanya thought she was going to cum thinking of her or because how she, herself, looked. But it quickly got to the point that it didn't matter. Jennifer said softly "I'm going to shoot."

"Towel sweetie.' And Jennifer exploded into the folds of the soft wet towel.

"Good girl. Now try and keep that thing under control until we get you dressed."

Jennifer had her head bowed but looked up to see Tanya holding some sexy white lingerie. "Suspender belt or hold ups?"

"Hold ups I think", said Jennifer. And Tanya handed her a pair with a deep lace band at the top, which she slipped up her legs.